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Healy made his Leinster debut at 19 years old in the 2006-07 season against Border Reivers, when he came of the bench.[4] He transitioned to first choice at his position for Leinster in the 2008-09 season. When as a 21 year old , Healy was a key part of the Leinster team that won the 2009 Heineken Cup in a 19–16 win against Leicester Tigers.

Healy continued to be a key player for Leinster in the following seasons, but struggled with a series of injuries, nearly retiring in the summer of 2015 after a neck injury.[8] However he managed to return to playing for Leinster, and after losing 10 kilos, regained his position as first choice in the 2017-2018 season, where he played a key role in Leinster winning its fourth European Cup against Racing 92, along with winning the Pro14 for the first time against the Scarlets. Healy is a member of an elite group of players to have won the European Cup four times, alongside teammates, Devin Toner, Jonathan Sexton and Isa Nacewa.[9]

Healy was named Man of the Match in a bruising encounter on 17 September 2011, when Ireland defeated Australia 15–6 at the 2011 Rugby World Cup in Eden Park.[17]

Healy was cited to appear before a disciplinary hearing in London on 13 February 2013, where he received a three-week suspension for stamping on the ankle of opponent player Dan Cole during Ireland's second round encounter with England in the Six Nations Championship.[18]

Healy was a key member of the Grand Slam winning Ireland team during the 2017-2018 6 Nations. Starting 4 of the 5 games including the decider against England in Twickenham.[19]